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Merck
CN

A9646

N-Acetylneuraminic acid

from sheep submaxillary glands, ≥99%

Synonym(s):

5-Acetamido-3,5-dideoxy-D-glycero-D-galactononulosonic acid, Lactaminic acid, NAN, NANA, Sialic acid

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About This Item

Empirical Formula (Hill Notation):
C11H19NO9
CAS Number:
131-48-6
Molecular Weight:
309.27
EC Number:
205-023-1
UNSPSC Code:
12352201
PubChem Substance ID:
24891482
Beilstein/REAXYS Number:
1716283
MDL number:
MFCD00006620

Key Documents

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InChI key

SQVRNKJHWKZAKO-PFQGKNLYSA-N

InChI

1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1

SMILES string

O[C@@]1(O[C@@]([C@@H]([C@H](C1)O)NC(C)=O)([H])[C@@H]([C@@H](CO)O)O)C(O)=O

biological source

sheep submaxillary glands

type

Type VIII

assay

≥99%

storage temp.

−20°C

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Biochem/physiol Actions

Both sialic acid and neuraminic acid are loosely used to refer to conjugates of neuraminic acid. N-Acetylneuraminic acid is often found as the terminal sugar of cell surface glycoproteins. Cell surface glycoproteins have important roles in cell recognition and interaction as well as in cell adhesion. Membrane glycoproteins are also important in tumor growth and metastases.

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
016K1485
048H0436
043H0036
020H0072
114H0396

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Influenza: Pathways to human adaptation.
David A Steinhauer
Nature, 499(7459), 412-413 (2013-07-19)
T A Timofeeva et al.
Voprosy virusologii, 58(1), 24-27 (2013-06-22)
The influenza virus hemagglutinin (HA) is an envelope virus glycoprotein responsible for the attachment of the virus particles to cells via binding terminal sialic acid residues of cell surface oligosaccharides. In our previous works on influenza A virus escape mutants
Wei Zhang et al.
Journal of virology, 87(10), 5949-5958 (2013-03-22)
Influenza A virus uses sialic acids as cell entry receptors, and there are two main receptor forms, α2,6 linkage or α2,3 linkage to galactose, that determine virus host ranges (mammalian or avian). The receptor binding hemagglutinins (HAs) of both 1918
Kannan Tharakaraman et al.
Cell, 153(7), 1475-1485 (2013-06-12)
Of the factors governing human-to-human transmission of the highly pathogenic avian-adapted H5N1 virus, the most critical is the acquisition of mutations on the viral hemagglutinin (HA) to "quantitatively switch" its binding from avian to human glycan receptors. Here, we describe
Sasirekha Ramani et al.
Journal of virology, 87(13), 7255-7264 (2013-04-26)
Naturally occurring bovine-human reassortant rotaviruses with a P[11] VP4 genotype exhibit a tropism for neonates. Interaction of the VP8* domain of the spike protein VP4 with sialic acid was thought to be the key mediator for rotavirus infectivity. However, recent
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